Too Good To Be True Ch. 28

Elaina had a great time posing in the various outfits. Though she did not model the "nude uniform". But yes, one of the approved 'uniforms' was the girls could just walk around naked doing what they needed. I was incredibly hard, having watched a hot Latina virgin member of the harem modeling all those outfits over her lacy lingerie.

I looked over at Cindy, "Well, I don't know how much time we have until Dinner, but I have an erection and you have a hymen. Those seem like two problems that can fix each other." I told her.

She squealed, "Let's do it! I am so horny."

"Lizzy doesn't care about watching, so we can leave her in the kitchen, but let's let the staff know if they want to watch, we can all go to the master suite and get Cindy fucked!" Courtney celebrated.

Berkley and Parker exchanged horny looks, then sent messages out to the staff. As Berkley led us to the bedroom, Brin, Nikki, and Mia joined us.

"Kat is watching monitors," Nikki told Parker.

"Good. Gotta have someone on duty." Parker affirmed.

Cindy threw off her clothes the instant we were in the bedroom, and Courtney and Tamora happily 'assisted' me in stripping, and I found myself, naked, and in bed with my very naked baby sister.

Don't think about the fact that she's your sister, I told myself, just realize she's a sexy virgin that wants your dick.

Cindy didn't want me to make the first move, kissing me passionately. Instinctively, I took command, driving her to lay down on her back as my hand massaged the small mounds of her tits, rolling her nipples in my hand as my tongue explored my sister's mouth. The breast stimulation led my sister to instinctively spread her legs. Cindy groaned and I slid my hand down to her aroused groin, though I initially avoided her pussy, straying as close as I could without actually touching her aching cunt. This only increased her arousal and made her crave it more. I slipped my mouth down to the breast my hand had vacated and began to lick and suck on her nipple, as my hand massaged her inner thigh.

A moan drew my attention to the rest of the girls in the room. My harem girls were mostly naked, pleasuring themselves, while the new staff girls, and Mary, were trying to pleasure themselves through their clothing. Only Elaina of the new staff stripped fully nude and was playing with her pussy and nipples as she watched me get ready to fuck Cindy. Taylor had a camera out recording the fucking.

This brought my erection to almost painful levels and I knew I needed to prep Cindy to get fucked fast. I finally gave in to Cindy's moaning request and started rubbing her soaking wet pussy. Her clitoris was so easy to find and she was already on the verge of orgasm and this pushed her over the edge into a screaming orgasm.

"Oh, FUCK! Oh, God! Tom, Please fuck me! Fuck your sister!" Cindy begged.

"Do you want me to be slow about breaking your hymen, or rip it like a bandaid?" I asked.

"Quick." She breathed, "I don't do pain well."

I could tell that the realization of the incestuous relationship happening in front of them affected several of the staff girls, but surprisingly for me, as opposed to making them back down, Nikki pulled up her shirt to get better access to her tits, sliding her hand under her bra to grope her tits. Parker put her hand into her pants, no longer satisfied with touching herself through her pants. Bridget also made the dive into her pants and put her hand up her shirt to grope her breasts.

I renewed my efforts playing with her clitoris, shifting to get in position to fuck her when she came. I could feel her building and getting excited as she saw my cock moving down toward her virgin tunnel. She started breathing fast, then came hard, screaming in pleasure.

I positioned my cock quickly at her entrance, rubbing it up and down her slit once, then pushed it in, immediately finding her hymen and driving through it. Again, like bubble wrap surrendering to my dick, her hymen tore.

"Oh, Fuck!" Cindy gasped, "It hurts, but feels... good at the same time. Give me more."

I gently rocked in and out of her, pressing inch after inch of my cock into her deflowered opening.

"Oh, fuck big brother. Your dick feels so good in my pussy." Cindy moaned.

If it wasn't clear before that we were currently engaged in incest Cindy was sure as fuck making it clear now. Oddly as my cock worked up to full-depth thrusts and Cindy had her first orgasm on my cock, the staff and girls only seemed to get more turned on.

I was so confused. Wasn't incest supposed to be looked down on and be viewed as gross, but here were all the girls in my harem plus the staff harem girls (God, I needed to figure out a better way of distinguishing them) all turned on as fuck watching me plow my sister's cunt.

Finally, I felt my climax rising and accelerated my plowing of my sister's snatch. With a deep thrust, I unloaded spewing half a dozen squirts of sperm and semen into her newly deflowered womanhood.

I pulled out and rolled off my sister and Taylor jumped up to take pictures.

"That was hot." Courtney laughed.

"It feels a little weird, especially since we had to come here to New Jersey so it would even be legal," I admitted.

The staff exchanged a glance.

I blinked, "You all just thought I was saying 'Oh well' and fucking my sister despite it being illegal?" I demanded.

Berkley laughed, "Okay, girls, raise your hands if you knew incest was illegal outside New Jersey."

"And Delaware!" Khloe added.

None of the staff members raised their hands.

"Who here cares if they continue?" The girls from the non-staff harem who had raised their hands acknowledging that they knew it was illegal lowered their hands.

"Okay, who thought it was hot?" Ali asked.

All the girls raised their hands, especially Cindy.

Parker laughed, "Besides, if they try to prosecute... who's gonna try to come after you for it and how would they prove it? I mean, we have camera surveillance footage of it here, but as you just said, it's legal in New Jersey. We'll make sure that no evidence of you two doing it outside of legal areas exists."

"Are you two gonna have kids?" Mia asked, a little concerned.

"No." Cindy acknowledged, "I'll have to find another man for that. The risks are bad and I don't want to worry about it."

"I'm sure that your brother can help you find some rich hot bachelor who will love you," Berkley assured her.

The girls who had stripped to enjoy the show got dressed and we headed down for dinner.

Berkley, Bridget, Bristol, and Amy acted as serving girls, though they had a seat at the table. They were evenly distributed along the table and brought the food out, ushering Lizzy to the table and making sure the drinks were full, and everyone was good.

Lizzy's food was delicious as always. Courtney sometimes helped her, and she was a good chef as well. Brittany had helped them do wonders in making sure the meals were nutritionally complete and good, which had seriously hampered Courtney until Lizzy showed her how to keep them delicious.

After dinner, the staff went their various ways, and the harem girls headed out to find their rooms and settle in.

Finding myself alone, I retired to my bedroom, the stains of Cindy's virginity still on my sheets. I stared at those blood spots. I thought about how I had literally JUST fucked my freaking sister... but I was really... okay with it? Cindy had enjoyed it. I hadn't harmed her. She was on birth control and wouldn't get pregnant. So we both had a good time, and no one was hurt. We were both consenting adults. It had to be okay, right? I mean, society said otherwise, but they would say the harem was wrong too.

I was interrupted in my musing by a firm knocking on the door. I opened the door and found Berkley standing there, still in the standard uniform of the Carmichael estate.

"May I come in?" Berkley asked nervously.

I was mildly concerned but let her in and closed the door.

"Is something wrong?" I asked.

"Oh, no! Nothing like that. Um... well, you see...." Berkly began, then took a deep breath. She blurted out something far too fast to follow.

"What?" I asked.

She took a deep breath, biting her lower lip. "I... came... here... so... you... can... fuck... me..." she repeated much more slowly, trembling with the jitters.

I smiled. "It's okay, Berkley, calm down. You would like to have sex with me?"

Berkley nodded anxiously.

I motioned to a chair. "Sit down, relax and let's talk."

Berkley quickly sat.

"Now, you seem uncomfortable. Is everything okay?" I began.

Berkley closed her eyes, "I... I'm uncomfortable around men..." she muttered with her eyes closed.

"Any reason?" I asked.

"Well, I grew up only having a sister, went to a girls-only private school, and..." she blurted out quickly, but I could follow this time. "...I have no idea what men are really like. I just graduated from college having avoided men, and at first, I got hired by Tabatha, one of Clarence's house managers. Then Clarence came to me, and... he was so understanding... and it sounded too good to be true..." she was hyperventilating.

"Slow down. Deep slow breaths." I told her.

Berkley followed my directions, keeping her eyes closed. When she was calm again she spoke again, "Sorry, with all the girls around, I could pretend you were just one of them. And it was hot watching you make love to your sister... and I could just be one of the girls..." Berkley was talking carefully, keeping her eyes closed.

"I... I want to make love to you... have you... well, fuck me, both vaginally and anally..." Berkley explained, "I want to lead the girls, and I've read about girls who are available to their man however he wants. I want... I want..."

She plowed forward, "I want to be sexy and feel like you want me. I want to feel naughty and... like one of your harem girls. I want you to be able to walk up behind me and just take me in the hall, in the lounges, when I'm cleaning, in the pool..."

She breathed. "I want to learn how to make you feel really good because I saw how you made Cindy feel earlier and I know you're going to do that for me. You've already given me so many opportunities... I want to pay you back in some way." She had to take some deep breaths.

"I want to show the rest of the staff that I can take the lead here and be the first to offer myself to you. I want to be the best executive housekeeper and harem girl combined into one sexy combo." She opened her eyes and looked at me. "So please... do me."

I tried not to drool, but damn, having girls throw themselves at me like this was always a major turn-on. I didn't feel like I was doing much, but what I did meant so much to these girls so they were willing to throw themselves naked at my feet, legs spread and fully available, and damn, for a guy who had just wanted to be faithful to Courtney, my girlfriend and future wife... I had more than twenty girls in my harem now!

"I'd be happy to, but there are a few things I'd like to discuss before we get too caught up in the moment," I told her.

"I'm on the pill, so you don't have to worry about condoms or pulling out." She informed me. "And when it comes to breaking my hymen, it seemed like Cindy really hurt when it happened, so go slow and I'll let you know when I'm ready for you to go again."

"Did you bring lube for anal, or should we use mine?" I asked.

"...lube?" She asked.

"Yes, lube. Lubricant. Your vagina produces liquids that keep friction from making sex... unpleasant. Your ass doesn't. So we have to use lube to make anal more pleasant." I told her.

"...oh... they don't usually..." she muttered.

"You watched porn for research?" I guessed.

She nodded.

"They usually cut out that part, but did you notice that their butts usually looked wet and shiny?" I asked.

She nodded again.

"That's because they lubed it off-screen," I explained.

"... oh... I'm glad you knew." She whispered.

"Who knows? Everyone is different and I could believe that some people don't need anal lube, but I wouldn't plan on it. We can also try lubing up in your pussy then moving to your ass, but if that lube fades we can't do it again without risk of yeast infections." I told her. "But there are some lubes, especially silicone-based ones, like the one I have, that last for hours, so you could lube yourself up and stay that way and I could just slide into your prepared anus."

Berkley seemed encouraged that her dream might be obtainable. "Anything else?"

"Is there anything you DON'T want me to do?" I asked her.

"Um, I was talking with some of the other girls and they said deepthroating is hard, so I don't think I'll go for that yet, but you can put your cock in and I'll try to suck it. But I plan on working with you on figuring that out over a longer period of time." She explained. "You see, I'm not sure yet if I'll ever be one of the girls wanting to bear your children, but I do plan on being your executive housekeeper and acting head of staff for a long time, and having sex with you... well, it's a really nice perk."

"Okay. Gentle on the oral sex today. Anything else?" I asked.

Berkley thought, "Um... I don't know. I'll let you know if you go anywhere I don't want you to, okay?"

"Sounds good." And I leaned forward and kissed her.

Unsurprisingly, she was not a great kisser. I'd definitely have to teach her how to kiss. But the sloppy surprised kiss of an inexperienced virgin was almost guaranteed to get me hard.

I moved in, helping her out of her jacket while slowly educating Berkley on how to kiss. She cooperated but didn't seem to know what to do, as I worked her buttons open, exposing her lacy white bra. Her clasp came undone easily and my mouth released her lips to suck on her virgin nipples.

Berkley moaned incoherently as my tongue circled her nipples, and I pulled her to me, lifting her and carrying her to the bed without releasing her nipple from my mouth. One hand began squeezing her other breast as I undid her pants with the other. I slowly worked her pants down until she kicked them off. Her matching lacy panties slipped off easily leaving her naked and ready to be fucked. I quickly shed my clothes and dove in to lick her pussy.

Berkley tried to speak as my tongue swirled on her clitoris, but words escaped her. She arched, pushing her pussy deeper into my face and my tongue caressed her hymen.

She reached down and pulled my head away from her. I sat back waiting for her to come down so she could speak.

"No..." she gasped. "I... want to feel it. Cindy said...that she could hardly feel you when you.... did it. I want to feel you make me a woman."

"It may hurt. I usually do try to break your hymen while you are in an orgasm to minimize the pain." I told her.

She shook her head. "If it hurts, I'll bear with it. I want to feel it when I become a woman."

"Okay." I accepted.

She spread her legs and let me move into position. Her pussy was soaked. I had made her very aroused and I rubbed my solid cock up and down her slit.

"What are you doing?" She asked.

"I'm getting some of your natural lubricant on my cock so it goes in nice," I told her.

She nodded and hitched her hips to try and make herself as available to me as possible.

I placed my now lubed head against her opening and slowly pushed it in, her womanhood opening to accept my rod. Her hymen caught the head of my penis, allowing no more than my tip to enter her. Berkley grabbed handfuls of the sheets.

"It's best if you relax," I told her.

She took a deep breath, released the sheets, and put her arms around my neck. I kissed her again, then asked her, "Are you ready?" She nodded and pulled me down for a kiss again.

I slowly began to push against her hymen, trying hard to make sure I didn't lurch into her when it broke. Berkley whimpered into the kiss. Her hymen stretched, doing its best to keep me out of her depths, and then I felt it start to give. Breaking it quickly felt like bubble wrap popping in your fingers, and breaking it slowly, I could feel the initial give then the rest of the membrane tear.

Berkley put a hand on my chest, gently pushing me back.

"Are you okay?" I asked.

"Other than my pussy getting split open?" She asked through a grimace, "Yep. Just need a second."

Her pussy juices and the blood of her virginity flowed around my throbbing cock. It felt so good, being just in her love tunnel. I could feel her pussy clenching and adjusting to the intrusion.

"Okay, try moving a little," Berkley instructed.

I pulled back just a touch and then pushed back in. I kept gently rocking, not wanting to go further until she confirmed she was good.

Berkley sat up and looked at her pelvis, seeing the tiny fraction of my cock that was actually entering her.

"It goes deeper?" She gasped.

"Yep, are you ready to fit more inside you?" I asked.

"Yes, just... slowly and gently." She instructed.

I kissed her and began caressing her breasts again, to approving moans, and slowly started opening her virgin pussy up. Thrust by thrust I buried my length into her, maybe a half inch deeper each thrust until I was hilt deep in her pussy. Her vagina was naturally deep enough to accept the whole length and potentially more if there was more dick to give, though I had no idea how much more she could handle. For all I knew another millimeter would bottom her out, but she could handle my entire length.

I began pinching her nipples lightly and thrusting slowly but deeply into her. Berkley moaned into the kiss, pulling me tight and accepting my gentle, but firm fucking. I slowly increased my pace, my thighs slapping against her ass.

Berkley broke the kiss, gasping for air and moaning, "Fuck me, Tom. I'm yours!"

I worked at a frenzied pace, plowing her hard and fast. She orgasmed and I latched onto her knack licking and sucking, not quite hard enough to leave a hickey and she responded enthusiastically. My climax rolled through my loins, and I released her neck.

"I'm going to fill you with my cum." I told her, making Berkley shudder.

I pushed my cock as deep into her pussy as I could, and I couldn't tell if I was just touching her cervix or if I managed to bottom out. My cock pulsed and my semen flooded her womb.

Berkley gasped, "Oh... Fuck..." She laid back feeling me fire the last sports of sperm into her newly opened pussy.

I was using every trick I knew to stay erect, and it wasn't working. I pulled my softening cock from her spasming cunt. It looked so sexy and I almost forgot to ask her if she wanted to do the traditional post-first-fuck photo.

"Oh, um... sure." Berkley conceded nervously.

I explained about the vaulting app we used and how secure it was.

"Oh, that's good to know and I'll be sure to let the staff know so they can prepare, mentally, for it." She spread her legs and posed as I directed.

The picture was taken, and we cuddled.

"You're still going to take my anal virginity too, right?" Berkley asked nervously.

"Yeah, I just need a few minutes for my dick to be ready to go again," I told her.

"You mean it can't just keep going?" Berkley asked, confused.

I explained about a guy's refractory period and how I had techniques to try to ignore it, but they weren't guaranteed to work.

"You could try giving me oral, or using your hand, but..." I referenced my blood, sperm, and pussy juice-covered cock.

Berkley conceded and we cuddled, me casually groping her tits and ass to keep her aroused as my cock recovered.

"So how many of the girls you've had in your harem have you done anal with?" Berkley asked.

"Well, Cindy and I hadn't done anything before we came here, and Mary is a probationary member, so we haven't really done anything." I started.

"What's up with that?" Berkley asked, confused as I twiddled her nipples.